Principal Software Engineer (AI Tooling & Adoption)
Posted Updated
- Fivetran is building data pipelines to power the modern data stack for thousands of companies
- Fivetran is seeking an exceptional Principal Software Engineer to lead our AI adoption initiative across the Engineering organization
- This unique leadership role combines deep technical expertise with strategic business acumen and change management capabilities
- You will be the driving force behind transforming our 500+ engineers into “Bionic Engineers” while implementing Virtual Engineer capabilities to achieve 10% productivity gains in FY26 and 20% in FY27
- As the single point of contact for AI initiatives in Engineering, you will orchestrate an engineering-wide transformation that makes AI-driven productivity a core engineering competency
- This role requires someone who can navigate the rapidly evolving AI landscape, drive adoption across diverse teams, and deliver measurable business impact
- This is a full-time position based out of our Oakland office
- Our hybrid work model offers a blend of remote flexibility and in-person collaboration, including two days in the office each week to connect and build as a team
- Technologies You’ll Use:
- Java, Postgres, Oracle, SQL Server, MySQL, Kubernetes, Docker, AWS, GCP, CircleCI
- Google Gemini, Anthropic Claude, Claude Code, ChatGPT, OpenAI Codex, GitHub Copilot
- Adoption Management & Leadership (40%):
- Drive Cultural Transformation: Lead the evolution from AI-curious to AI-native engineering practices across all teams
- Champion Change Management: Convert skeptics into advocates through data-driven demonstrations of value and hands-on enablement
- Measure & Accelerate Adoption: Establish KPIs, track progress from the current 50% to 100% adoption, and implement interventions to accelerate uptake
- Build Communities of Practice: Create forums for knowledge sharing, celebrate wins, and foster peer-to-peer learning
- Technical Leadership (35%):
- Tool Evaluation & Selection: Continuously assess emerging AI tools (Copilot, Claude Code, Codex, etc.) and make data-driven recommendations
- Architecture & Integration: Design technical frameworks for integrating AI tools into existing development workflows and CI/CD pipelines
- Virtual Engineer Implementation: Lead proof-of-concepts for coding agents in standardized tasks (Lite Connectors via CoIL, code refactoring, test generation)
- Security & Compliance: Partner with Security and Legal teams to ensure AI tool usage protects IP and meets compliance requirements
- Technical Standards: Establish best practices, guidelines, and guardrails for AI-assisted development
- Performance Optimization: Analyze and optimize the technical performance and cost-efficiency of AI tool deployments
- Innovation Pipeline: Maintain awareness of cutting-edge AI developments and identify opportunities for competitive advantage
- Business Leadership (25%):
- Strategic Planning: Develop and execute the three-phase AI adoption roadmap (Explore & Learn → Enable, Train & Adopt → Core Competency)
- Budget Management: Oversee $1M+ annual tool budget, optimize spend across 500+ team members, and demonstrate ROI
- Stakeholder Management: Build relationships with the CEO, Engineering Leadership, Finance, L&D, Legal, and Security teams
- Business Case Development: Quantify productivity gains, cost savings, and strategic value of AI initiatives
- Vendor Relations: Negotiate enterprise contracts, manage vendor relationships, and influence product roadmaps
- Cross-functional Collaboration: Work with Program Managers, Engineering Managers, and other non-IC roles to extend AI benefits
- Competitive Intelligence: Monitor industry trends and ensure Fivetran maintains a leadership position in AI-augmented engineering
- Enable Success at Scale: Design and implement adoption playbooks that work across diverse teams with varying technical backgrounds
- Remove Barriers: Identify and systematically eliminate technical, cultural, and process obstacles to AI adoption
- Communicate Impact: Regularly present adoption metrics, success stories, and ROI to engineering leadership and executives
- Track record of evaluating and implementing new technologies at scale
- Experience with CI/CD, DevOps practices, and modern software development workflows
- Deep hands-on experience with AI-powered development tools (GitHub Copilot, ChatGPT, Claude, etc.)
- 10+ years of software engineering experience with proven expertise across multiple programming languages and paradigms
- Strong understanding of LLMs, prompt engineering, and AI model capabilities/limitations
- Track record of successful change management in engineering contexts
- Experience leading without authority and influencing senior technical leaders
- Demonstrated ability to convert technical innovations into business value
- Proven ability to drive technical initiatives across large engineering organizations (500+ people)
- Experience presenting to C-level executives and board members
- Data-driven approach to measuring and improving adoption metrics
- Experience driving tool adoption across diverse technical teams
- Patience and empathy when working with skeptics and late adopters
- Strong communication skills with the ability to create compelling narratives for different audiences
- Track record of building training programs and enablement materials
- Background in developer productivity, platform engineering, or DevEx roles
- Experience with Fivetran’s tech stack (Java, Python, C, SQL, Bazel, React)
- Experience with virtual agents/coding assistants in production environments
- Knowledge of AI/ML fundamentals and enterprise AI governance
- Previous experience in high-growth SaaS companies
Skills
- AI
- Ai Enablement
- Anthropic
- AWS
- ChatGPT
- CI/CD
- CircleCI
- Claude
- Claude Code
- Data Pipelines
- DevOps
- Docker
- Fivetran
- GCP
- Gemini
- GitHub
- Github Copilot
- Java
- Kubernetes
- LLM
- Machine Learning
- MySQL
- OpenAI
- Oracle
- PostgreSQL
- Prompt Engineering
- Python
- React
- SaaS
- SQL
- SQL Server
- Stakeholder Management
- Strategic Planning